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Volumn , Issue 20, 2007, Pages 3209-3213

Polymer-incarcerated palladium with active phosphine as recoverable and reusable Pd catalyst for the amination of aryl chlorides

(4) Inasaki, Takeshi a Ueno, Masaharu a Miyamoto, Shinpei a Kobayashi, Shu a

a UNIVERSITY OF TOKYO (Japan)

Author keywords

Aminations; Aryl chlorides; Heterogeneous catalysis; Palladium; Polymer

Indexed keywords

AMINE; CHLORIDE; LIGAND; PALLADIUM; PHOSPHINE; POLYMER;

ADDITION REACTION; AMINATION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL STRUCTURE; CROSS LINKING; MICROENCAPSULATION;

EID: 37749042148 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2007-1000816 Document Type: Article

Times cited : (18)

References (53)

1
- 0003441482
- Wiley: Chichester
- (a) Tsuji, J. Palladium Reagents and Catalysts; Wiley: Chichester, 1995.
- (1995) Palladium Reagents and Catalysts
- Tsuji, J.¹

2
- 0003995267
- Negishi, E, Ed, John Wiley and Sons: New York
- (b) Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., Ed.; John Wiley and Sons: New York, 2002.
- (2002) Handbook of Organopalladium Chemistry for Organic Synthesis

3
- 4143153074
- (c) Stahl, S. S. Angew. Chem. Int. Ed. 2004, 43, 3400.
- (2004) Angew. Chem. Int. Ed , vol.43 , pp. 3400
- Stahl, S.S.¹

4
- 33846893890
- (a) Yin, L. X.; Liebscher, J. Chem. Rev. 2007, 107, 133.
- (2007) Chem. Rev , vol.107 , pp. 133
- Yin, L.X.¹ Liebscher, J.²

5
- 18244362298
- (b) Kwon, M. S.; Kim, N.; Park, C. M.; Lee, J. S.; Kang, K. Y.; Park, J. Org. Lett. 2005, 7, 1077.
- (2005) Org. Lett , vol.7 , pp. 1077
- Kwon, M.S.¹ Kim, N.² Park, C.M.³ Lee, J.S.⁴ Kang, K.Y.⁵ Park, J.⁶

6
- 4444383970
- (c) Kim, N.; Kwon, M. S.; Park, C. M.; Park, J. Tetrahedron Lett. 2004, 45, 7057.
- (2004) Tetrahedron Lett , vol.45 , pp. 7057
- Kim, N.¹ Kwon, M.S.² Park, C.M.³ Park, J.⁴

7
- 0037184451
- (d) Choudary, B. M.; Madhi, S.; Chowdari, N. S.; Kantam, M. L.; Sreedhar, B. J. Am. Chem. Soc. 2002, 124, 14127.
- (2002) J. Am. Chem. Soc , vol.124 , pp. 14127
- Choudary, B.M.¹ Madhi, S.² Chowdari, N.S.³ Kantam, M.L.⁴ Sreedhar, B.⁵

8
- 0141852891
- (a) Lin, C.-A.; Luo, F.-T. Tetrahedron Lett. 2003, 44, 7565.
- (2003) Tetrahedron Lett , vol.44 , pp. 7565
- Lin, C.-A.¹ Luo, F.-T.²

9
- 20444409746
- (b) Luo, F.-T.; Xue, C.; Ko, S.-L.; Shao, Y.-D.; Wu, C.-J.; Kuo, Y.-M. Tetrahedron 2005, 61, 6040.
- (2005) Tetrahedron , vol.61 , pp. 6040
- Luo, F.-T.¹ Xue, C.² Ko, S.-L.³ Shao, Y.-D.⁴ Wu, C.-J.⁵ Kuo, Y.-M.⁶

10
- 0037433605
- (c) Chauhan, B. P.; Rathore, J. S.; Chauhan, M.; Krawicz, A. J. Am. Chem. Soc. 2003, 125, 2876.
- (2003) J. Am. Chem. Soc , vol.125 , pp. 2876
- Chauhan, B.P.¹ Rathore, J.S.² Chauhan, M.³ Krawicz, A.⁴

11
- 0035840198
- (d) Biffs, A.; Zecca, M.; Basato, M. J. Mol. Catal. A: Chem. 2001, 173, 249.
- (2001) J. Mol. Catal. A: Chem , vol.173 , pp. 249
- Biffs, A.¹ Zecca, M.² Basato, M.³

12
- 8444230920
- (a) Tsang, C.-W.; Baharloo, B.; Riendl, D.; Yam, M.; Gates, D. P. Angew. Chem. Int. Ed. 2004, 43, 5682.
- (2004) Angew. Chem. Int. Ed , vol.43 , pp. 5682
- Tsang, C.-W.¹ Baharloo, B.² Riendl, D.³ Yam, M.⁴ Gates, D.P.⁵

13
- 33751302519
- (b) Li, J.-H.; Hu, X.-C.; Xie, Y.-X. Tetrahedron Lett. 2006, 47, 9239.
- (2006) Tetrahedron Lett , vol.47 , pp. 9239
- Li, J.-H.¹ Hu, X.-C.² Xie, Y.-X.³

14
- 33644998342
- (c) He, H. S.; Yan, J. J.; Shen, R.; Zhuo, S.; Toy, P. H. Synlett 2006, 563.
- (2006) Synlett , pp. 563
- He, H.S.¹ Yan, J.J.² Shen, R.³ Zhuo, S.⁴ Toy, P.H.⁵

15
- 0037430562
- (d) Yamada, Y. M. A.; Takeda, K.; Takahashi, H.; Ikegami, S. Tetrahedron Lett. 2003, 44, 2379.
- (2003) Tetrahedron Lett , vol.44 , pp. 2379
- Yamada, Y.M.A.¹ Takeda, K.² Takahashi, H.³ Ikegami, S.⁴

16
- 0036458241
- (a) Yamada, Y. M. A.; Tabata, H.; Takahashi, H.; Ikegami, S. Synlett 2002, 2031.
- (2002) Synlett , pp. 2031
- Yamada, Y.M.A.¹ Tabata, H.² Takahashi, H.³ Ikegami, S.⁴

17
- 33749005084
- (b) Zhang, Z.; Wang, Z. J Org. Chem. 2006, 71, 7485.
- (2006) J Org. Chem , vol.71 , pp. 7485
- Zhang, Z.¹ Wang, Z.²

18
- 33846922255
- (c) Singh, G.; Bali, S.; Singh, A. K. Polyhedron 2006, 26, 897.
- (2006) Polyhedron , vol.26 , pp. 897
- Singh, G.¹ Bali, S.² Singh, A.K.³

19
- 0034832488
- (d) Djakovitch, L.; Koehler, K. J. Am. Chem. Soc. 2001, 123, 5990.
- (2001) J. Am. Chem. Soc , vol.123 , pp. 5990
- Djakovitch, L.¹ Koehler, K.²

20
- 0035356045
- (a) Parrish, C. A.; Buchwald, S. L. J. Org. Chem. 2001, 66, 3820.
- (2001) J. Org. Chem , vol.66 , pp. 3820
- Parrish, C.A.¹ Buchwald, S.L.²

21
- 25444506884
- (b) Guinó, M.; Hii, K. K. Tetrahedron Lett. 2005, 46, 7363.
- (2005) Tetrahedron Lett , vol.46 , pp. 7363
- Guinó, M.¹ Hii, K.K.²

22
- 34250026737
- (c) Leyva, A.; García, H.; Corma, A. Tetrahedron 2007, 63, 7097.
- (2007) Tetrahedron , vol.63 , pp. 7097
- Leyva, A.¹ García, H.² Corma, A.³

23
- 34547807273
- (d) Nishio, R.; Sugiura, M.; Kobayashi, S. Chem. Asian J. 2007, 2, 983.
- (2007) Chem. Asian J , vol.2 , pp. 983
- Nishio, R.¹ Sugiura, M.² Kobayashi, S.³

24
- 0034671512
- To the best of our knowledge reports on the amination of aryl chlorides using immobilized Pd catalysts have been very limited, and in no case, except in ref. 6d, was information relating to Pd leaching reported. On the other hand, Lipshutz et al. reported Ni/C catalysis for the amination: Lipshutz, B. H, Ueda, H. Angew. Chem. Int. Ed. 2000, 39, 4492
- (e) To the best of our knowledge reports on the amination of aryl chlorides using immobilized Pd catalysts have been very limited, and in no case, except in ref. 6d, was information relating to Pd leaching reported. On the other hand, Lipshutz et al. reported Ni/C catalysis for the amination: Lipshutz, B. H.; Ueda, H. Angew. Chem. Int. Ed. 2000, 39, 4492.

25
- 0037458972
- (f) Lipshutz, B. H.; Tasler, S.; Chrisman, W.; Spliethoff, B.; Tesche, B. J. Org. Chem. 2003, 68, 1177.
- (2003) J. Org. Chem , vol.68 , pp. 1177
- Lipshutz, B.H.¹ Tasler, S.² Chrisman, W.³ Spliethoff, B.⁴ Tesche, B.⁵

26
- 0037458782
- (g) Tasler, S.; Lipshutz, B. H. J. Org. Chem. 2003, 68, 1190.
- (2003) J. Org. Chem , vol.68 , pp. 1190
- Tasler, S.¹ Lipshutz, B.H.²

27
- 0037467379
- Polymer incarcerated catalysts: (a) Akiyama, R.; Kobayashi, S. J. Am. Chem. Soc. 2003, 125, 3412.
- Polymer incarcerated catalysts: (a) Akiyama, R.; Kobayashi, S. J. Am. Chem. Soc. 2003, 125, 3412.

28
- 25444528759
- (b) Takeuchi, M.; Akiyama, R.; Kobayashi, S. J. Am. Chem. Soc. 2005, 127, 13096.
- (2005) J. Am. Chem. Soc , vol.127 , pp. 13096
- Takeuchi, M.¹ Akiyama, R.² Kobayashi, S.³

29
- 27644547449
- (c) Nishio, R.; Sugiura, M.; Kobayashi, S. Org. Lett. 2005, 7, 4831.
- (2005) Org. Lett , vol.7 , pp. 4831
- Nishio, R.¹ Sugiura, M.² Kobayashi, S.³

30
- 32644431645
- (d) Hagio, H.; Sugiura, M.; Kobayashi, S. Org. Lett. 2006, 8, 375.
- (2006) Org. Lett , vol.8 , pp. 375
- Hagio, H.¹ Sugiura, M.² Kobayashi, S.³

31
- 13944266675
- (e) Okamoto, K.; Akiyama, R.; Yoshida, H.; Yoshida, T.; Kobayashi, S. J. Am. Chem. Soc. 2005, 127, 2125.
- (2005) J. Am. Chem. Soc , vol.127 , pp. 2125
- Okamoto, K.¹ Akiyama, R.² Yoshida, H.³ Yoshida, T.⁴ Kobayashi, S.⁵

32
- 21244475885
- (f) Kobayashi, S.; Miyamura, H.; Akiyama, R.; Ishida, T. J. Am. Chem. Soc. 2005, 127, 9251.
- (2005) J. Am. Chem. Soc , vol.127 , pp. 9251
- Kobayashi, S.¹ Miyamura, H.² Akiyama, R.³ Ishida, T.⁴

33
- 0001038733
- (a) Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805.
- (1998) Acc. Chem. Res , vol.31 , pp. 805
- Wolfe, J.P.¹ Wagaw, S.² Marcoux, J.-F.³ Buchwald, S.L.⁴

34
- 0029743317
- (b) Wolfe, J. P.; Wagaw, S.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 7215.
- (1996) J. Am. Chem. Soc , vol.118 , pp. 7215
- Wolfe, J.P.¹ Wagaw, S.² Buchwald, S.L.³

35
- 0000037108
- (c) Hartwig, J. F. Acc. Chem. Res. 1998, 31, 852.
- (1998) Acc. Chem. Res , vol.31 , pp. 852
- Hartwig, J.F.¹

36
- 0032560932
- (a) Old, D. W.; Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 9722.
- (1998) J. Am. Chem. Soc , vol.120 , pp. 9722
- Old, D.W.¹ Wolfe, J.P.² Buchwald, S.L.³

37
- 0033549829
- (b) Wolfe, J. P.; Buchwald, S. L. Angew. Chem. Int. Ed. 1999, 38, 2413.
- (1999) Angew. Chem. Int. Ed , vol.38 , pp. 2413
- Wolfe, J.P.¹ Buchwald, S.L.²

38
- 0034712156
- (c) Wolfe, J. P.; Tomori, H.; Sadighi, J. P.; Yin, J.; Buchwald, S. L. J. Org. Chem. 2000, 65, 1158.
- (2000) J. Org. Chem , vol.65 , pp. 1158
- Wolfe, J.P.¹ Tomori, H.² Sadighi, J.P.³ Yin, J.⁴ Buchwald, S.L.⁵

39
- 0035917354
- (d) Ali, M. H.; Buchwald, S. L. J. Org. Chem. 2001, 66, 2560.
- (2001) J. Org. Chem , vol.66 , pp. 2560
- Ali, M.H.¹ Buchwald, S.L.²

40
- 0041996505
- (e) Zim, D.; Buchwald, S. L. Org. Lett. 2003, 5, 2413.
- (2003) Org. Lett , vol.5 , pp. 2413
- Zim, D.¹ Buchwald, S.L.²

41
- 24944477864
- (f) Charles, M. D.; Schultz, P.; Buchwald, S. L. Org. Lett. 2005, 7, 3965.
- (2005) Org. Lett , vol.7 , pp. 3965
- Charles, M.D.¹ Schultz, P.² Buchwald, S.L.³

42
- 0032578172
- (g) Hamann, B. C.; Hartwig, J. F. J. Am. Chem. Soc. 1998, 120, 7369.
- (1998) J. Am. Chem. Soc , vol.120 , pp. 7369
- Hamann, B.C.¹ Hartwig, J.F.²

43
- 0034682151
- (h) Stauffer, S. R.; Lee, S.; Stambuli, J. P.; Hauck, S. I.; Hartwig, J. F. Org. Lett. 2000, 2, 1423.
- (2000) Org. Lett , vol.2 , pp. 1423
- Stauffer, S.R.¹ Lee, S.² Stambuli, J.P.³ Hauck, S.I.⁴ Hartwig, J.F.⁵

44
- 14844330054
- (i) Shen, Q.; Shekhar, S.; Stambuli, J. P.; Hartwig, J. F. Angew. Chem. Int. Ed. 2005, 44, 1371.
- (2005) Angew. Chem. Int. Ed , vol.44 , pp. 1371
- Shen, Q.¹ Shekhar, S.² Stambuli, J.P.³ Hartwig, J.F.⁴

45
- 33746931578
- (j) Shen, Q.; Hartwig, J. F. J. Am. Chem. Soc. 2006, 128, 10028.
- (2006) J. Am. Chem. Soc , vol.128 , pp. 10028
- Shen, Q.¹ Hartwig, J.F.²

46
- 34247486915
- Barder, T. E.; Buchwald, S. L. J. Am. Chem. Soc. 2007, 129, 5096.
- (2007) J. Am. Chem. Soc , vol.129 , pp. 5096
- Barder, T.E.¹ Buchwald, S.L.²

47
- 37749034912
- Microencapsulated catalysts: (a) Kobayashi, S.; Nagayama, S. J. Am. Chem. Soc. 1998, 120, 2985.
- Microencapsulated catalysts: (a) Kobayashi, S.; Nagayama, S. J. Am. Chem. Soc. 1998, 120, 2985.

48
- 0000683716
- (b) Nagayama, S.; Endo, M.; Kobayashi, S. J. Org. Chem. 1998, 63, 6094.
- (1998) J. Org. Chem , vol.63 , pp. 6094
- Nagayama, S.¹ Endo, M.² Kobayashi, S.³

49
- 0033537034
- (c) Kobayashi, S.; Endo, M.; Nagayama, S. J. Am. Chem. Soc. 1999, 121, 11229.
- (1999) J. Am. Chem. Soc , vol.121 , pp. 11229
- Kobayashi, S.¹ Endo, M.² Nagayama, S.³

50
- 0000600955
- (d) Kobayashi, S.; Ishida, T.; Akiyama, R. Org. Lett. 2001, 3, 2649.
- (2001) Org. Lett , vol.3 , pp. 2649
- Kobayashi, S.¹ Ishida, T.² Akiyama, R.³

51
- 0035903603
- (e) Akiyama, R.; Kobayashi, S. Angew. Chem. Int. Ed. 2001, 40, 3469.
- (2001) Angew. Chem. Int. Ed , vol.40 , pp. 3469
- Akiyama, R.¹ Kobayashi, S.²

52
- 0037099191
- (f) Akiyama, R.; Kobayashi, S. Angew. Chem. Int. Ed. 2002, 41, 2602.
- (2002) Angew. Chem. Int. Ed , vol.41 , pp. 2602
- Akiyama, R.¹ Kobayashi, S.²

53
- 37749010287
- Preparation of Copolymer 1: Styrene (2.24 g, 21.6 mmol, 2, 2-phenylallyloxy)methyl]oxirane (630 mg, 3.32 mmol, tetraethyleneglycol mono-2-phenyl-2-propenyl ether (1.03 g, 3.32 mmol, dicyclohexyl-2-[4′-(4- styrylmethoxy)phenyl]phenylphosphine (2.40 g, 4.97 mmol) and 2,2′-azobis(isobutyronitrile, 54.4 mg, 0.332 mmol) were mixed in CHCl3 (4.2 mL, The mixture was stirred at reflux for 27 h under argon and was then cooled to r.t. The resulting polymer solution was poured slowly into hot deoxygenated hexane and the precipitated polymer was collected by filtration and washed with hexane. The polymer so obtained was dissolved in CHCl3, and the resulting solution was poured slowly into MeCN. The precipitated polymer was filtered and washed with MeCN several times and dried in vacuo to afford the desired copolymer 1 (3.67 g, 58, The molar ratio of the monomer was determined by 1H NMR analysis {styrene-2, 2-phenylallyloxy)methyl
- 2O and MeOH and was then dried in vacuo. The catalyst was reused without any other purification step.

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